1. Field of the Invention
This invention relates to a process for isomerizing olefinically unsaturated secondary alcohols to saturated ketones.
2. Description of the Related Art
A number of methods of isomerizing olefinically unsaturated secondary alcohols are known in the art. U.S. Pat. No. 2,178,760 discloses a process for catalytically isomerizing a hydroxy carboxylic acid or its functional derivative comprising heating the carboxylic acid or its functional derivative of a carboxylic acid in the presence of a nickel catalyst prepared by reducing an oxygen-containing nickel compound with hydrogen. U.S. Pat. No. 2,340,745 discloses a process for catalytically isomerizing a ricinoleic compound comprising heating a ricinoleic compound in the presence of an elementary nickel or cobalt catalyst. U.S. Pat. No. 2,847,432 discloses a method of oxidizing an alkyl ester of 12-ketostearic acid comprising reacting the ester with nitric acid in the presence of a mixed catalyst containing a copper tearing material. Japanese Kokai 73 48,417 (Chemical Abstracts 79:125878e) discloses the isomerization of unsaturated hydroxy fatty acids and their esters by heating the unsaturated hydroxy fatty acids and their esters in the presence of copper, nickel, or palladium. The Journal of the American Oil Chemists Society Vol 42, pages 340-344 1965) describes a method of preparing methyl 12-ketostearate by heating methyl ricinoleate over Raney nickel catalyst for about one-half hour. The Journal of Oil Technologists' Association of India, pages 61-64July/September 1976 describes the production of keto stearic acids through the hydrogenation of castor oil in the presence of Raney Nickel. Maslobiona Zhirovoa Delo. 13, (2) 13-14 (1937) (Chemical Abstracts 31, 7397) describes a method of preparing 12-ketostearic acid by heating castor oil in a CO.sub.2 atmosphere in the presence of nickel, copper, and platinum black catalysts. The preparation of 12-ketostearic acid by isomerizing methyl ricinoleate over raney nickel is described in Bull. Soc. Chim. France, pages 339-42 (1954) (Chemical Abstracts 49, 4520 c). French patent No. 1,043,797 (Chemical Abstracts 52, 11908 b) discloses a method of preparing methyl 12-oxostearate by reducing methyl ricinoleate with hydrogen over a Cu-ZrO.sub.2 catalyst.
None of the prior art methods discloses a substantially fully hydrogenated catalyst. All of prior art methods suffer from the disadvantage that a substantial amount of the saturated hydroxy compound or the unsaturated keto compound is formed along with the desired saturated keto compound.